This page lists the head-to-head record of Chelsea vs Middlesbrough including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Middlesbrough | Chelsea | Draws |
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| Total Matches | 96 | 25 | 46 | 25 |
| At Riverside Stadium | 47 | 4 | 32 | 11 |
| At Stamford Bridge | 49 | 21 | 14 | 14 |
| FA Cup Matches | 2 | 0 | 2 | 0 |
| Carling Cup Matches | 2 | 1 | 1 | 0 |
| Premier League Matches | 92 | 24 | 43 | 25 |
| Total Goals Scored | 258 | 105 | 153 | |
Last 50 Middlesbrough vs Chelsea Matches
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| 2024 23 January | | Carling Cup | Chelsea | 6 - 1 | Middlesbrough |
| 2024 9 January | | Carling Cup | Middlesbrough | 1 - 0 | Chelsea |
| 2022 19 March | | FA Cup | Middlesbrough | 0 - 2 | Chelsea |
| 2017 8 May | | Premier League | Chelsea | 3 - 0 | Middlesbrough |
| 2016 20 November | | Premier League | Middlesbrough | 0 - 1 | Chelsea |
| 2013 27 February | | FA Cup | Middlesbrough | 0 - 2 | Chelsea |
| 2009 28 January | | Premier League | Chelsea | 2 - 0 | Middlesbrough |
| 2008 18 October | | Premier League | Middlesbrough | 0 - 5 | Chelsea |
| 2008 30 March | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 2007 20 October | | Premier League | Middlesbrough | 0 - 2 | Chelsea |
| 2007 10 February | | Premier League | Chelsea | 3 - 0 | Middlesbrough |
| 2006 23 August | | Premier League | Middlesbrough | 2 - 1 | Chelsea |
| 2006 10 February | | Premier League | Middlesbrough | 3 - 0 | Chelsea |
| 2005 2 December | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 2005 3 January | | Premier League | Chelsea | 2 - 0 | Middlesbrough |
| 2004 24 September | | Premier League | Middlesbrough | 0 - 1 | Chelsea |
| 2004 9 April | | Premier League | Chelsea | 0 - 0 | Middlesbrough |
| 2003 4 October | | Premier League | Middlesbrough | 1 - 2 | Chelsea |
| 2002 13 December | | Premier League | Middlesbrough | 1 - 1 | Chelsea |
| 2002 15 November | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 2002 26 April | | Premier League | Middlesbrough | 0 - 2 | Chelsea |
| 2001 22 September | | Premier League | Chelsea | 2 - 2 | Middlesbrough |
| 2001 30 March | | Premier League | Chelsea | 2 - 1 | Middlesbrough |
| 2000 15 December | | Premier League | Middlesbrough | 1 - 0 | Chelsea |
| 2000 21 April | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1999 24 September | | Premier League | Middlesbrough | 0 - 1 | Chelsea |
| 1999 13 April | | Premier League | Middlesbrough | 0 - 0 | Chelsea |
| 1998 25 September | | Premier League | Chelsea | 2 - 0 | Middlesbrough |
| 1997 21 March | | Premier League | Middlesbrough | 1 - 0 | Chelsea |
| 1996 20 August | | Premier League | Chelsea | 1 - 0 | Middlesbrough |
| 1996 3 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
| 1995 25 August | | Premier League | Middlesbrough | 2 - 0 | Chelsea |
| 1993 2 April | | Premier League | Chelsea | 4 - 0 | Middlesbrough |
| 1992 10 December | | Premier League | Middlesbrough | 0 - 0 | Chelsea |
| 1979 20 April | | Premier League | Chelsea | 2 - 1 | Middlesbrough |
| 1978 15 December | | Premier League | Middlesbrough | 7 - 2 | Chelsea |
| 1978 3 April | | Premier League | Middlesbrough | 2 - 0 | Chelsea |
| 1977 14 October | | Premier League | Chelsea | 0 - 0 | Middlesbrough |
| 1975 21 March | | Premier League | Chelsea | 1 - 2 | Middlesbrough |
| 1974 6 September | | Premier League | Middlesbrough | 1 - 1 | Chelsea |
| 1954 5 March | | Premier League | Middlesbrough | 3 - 3 | Chelsea |
| 1953 16 October | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1953 17 April | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1952 28 November | | Premier League | Middlesbrough | 4 - 0 | Chelsea |
| 1952 15 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
| 1951 5 October | | Premier League | Middlesbrough | 0 - 0 | Chelsea |
| 1950 22 December | | Premier League | Chelsea | 1 - 1 | Middlesbrough |
| 1950 25 August | | Premier League | Middlesbrough | 3 - 0 | Chelsea |
| 1950 28 March | | Premier League | Chelsea | 2 - 1 | Middlesbrough |
| 1949 25 November | | Premier League | Middlesbrough | 2 - 1 | Chelsea |
Biggest Middlesbrough Victory vs Chelsea
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| 1978 15 December | | Premier League | Middlesbrough | 7 - 2 | Chelsea |
Biggest Chelsea Victory vs Middlesbrough
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| 1952 15 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
Biggest Middlesbrough Defeat vs Chelsea
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| 1952 15 February | | Premier League | Chelsea | 5 - 0 | Middlesbrough |
Biggest Chelsea Defeat vs Middlesbrough
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| 1978 15 December | | Premier League | Middlesbrough | 7 - 2 | Chelsea |
Last 5 Middlesbrough Home Matches
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| 2025 25 October | | Championship | Middlesbrough | 1 - 1 | Wrexham |
| 2025 17 October | | Championship | Middlesbrough | 2 - 1 | Ipswich Town |
| 2025 30 September | | Championship | Middlesbrough | 0 - 0 | Stoke City |
| 2025 19 September | | Championship | Middlesbrough | 2 - 1 | West Bromwich Albion |
| 2025 30 August | | Championship | Middlesbrough | 1 - 0 | Sheffield United |
Last 5 Chelsea Home Matches
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| 2025 25 October | | Premier League | Chelsea | 1 - 2 | Sunderland |
| 2025 22 October | | UEFA Champions League | Chelsea | 5 - 1 | Ajax |
| 2025 4 October | | Premier League | Chelsea | 2 - 1 | Liverpool |
| 2025 30 September | | UEFA Champions League | Chelsea | 1 - 0 | Benfica |
| 2025 27 September | | Premier League | Chelsea | 1 - 3 | Brighton & Hove Albion |
Last 5 Middlesbrough Away Matches
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| 2025 22 October | | Championship | Sheffield Wednesday | 0 - 1 | Middlesbrough |
| 2025 4 October | | Championship | Portsmouth | 1 - 0 | Middlesbrough |
| 2025 27 September | | Championship | Southampton | 1 - 1 | Middlesbrough |
| 2025 13 September | | Championship | Preston North End | 2 - 2 | Middlesbrough |
| 2025 23 August | | Championship | Norwich City | 1 - 2 | Middlesbrough |
Last 5 Chelsea Away Matches
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| 2025 18 October | | Premier League | Nottingham Forest | 0 - 3 | Chelsea |
| 2025 23 September | | Carling Cup | Lincoln City | 1 - 2 | Chelsea |
| 2025 20 September | | Premier League | Manchester United | 2 - 1 | Chelsea |
| 2025 17 September | | UEFA Champions League | Bayern Munchen | 3 - 1 | Chelsea |
| 2025 13 September | | Premier League | Brentford | 2 - 2 | Chelsea |